744212-68-8
744212-68-8 结构式
基本信息
1-Benzyl-5-(hydroxyMethyl)piperidin-2-one
2-Piperidinone,5-(hydroxymethyl)-1-(phenylmethyl)-
16,17-BIS(OCTYLOXY)ANTHRA[9,1,2-CDE]BENZO[RST]PENTAPHENE-5,10-DIO
物理化学性质
制备方法
156779-11-2
744212-68-8
以1-苄基-6-氧代哌啶-3-甲酸甲酯为原料合成1-苄基-5-(羟甲基)哌啶-2-酮的一般步骤：将化合物1-苄基-6-氧代哌啶-3-甲酸甲酯（5.23 g，23.85 mmol）溶于无水THF（35 mL）中，冷却至0℃。在搅拌下加入LiBH4（1.04 g，47.70 mmol），随后将反应混合物缓慢升温至室温并搅拌过夜。反应完成后，在0℃下用水（20 mL）淬灭反应，随后加入10% HCl溶液调节pH。用EtOAc（4×20 mL）萃取水层，合并有机层，用无水MgSO4干燥，过滤后减压浓缩。粗产物通过硅胶柱色谱法（洗脱剂：环己烷/EtOAc，60:40）纯化，得到1-苄基-5-(羟甲基)哌啶-2-酮（4.03 g，收率77%）为透明油状物（Rf = 0.11，环己烷/EtOAc，50:50）。1H NMR (600 MHz, CDCl3) δ 7.33-7.18 (m, 5H, PhH), 4.59 (d, J = 14.6 Hz, 1H, PhCH2), 4.53 (d, J = 14.6 Hz, 1H, PhCH2), 3.53 (dd, J = 10.7, 5.6 Hz, 1H, CH2OH), 3.44 (dd, J = 10.7, 7.2 Hz, 1H, CH2OH), 3.30 (ddd, J = 12.2, 5.2, 1.5 Hz, 1H, NCH2), 2.99 (dd, J = 12.2, 10.1 Hz, 1H, NCH2), 2.92 (br s, 1H, OH), 2.51 (ddd, J = 17.8, 5.8, 3.4 Hz, 1H, C=OCH2), 2.39 (ddd, J = 17.8, 11.3, 6.5 Hz, 1H, C=OCH2), 2.04-1.95 (m, 1H, OHCH2CH), 1.89-1.82 (m, 1H, C=OCH2CH2), 1.54-1.46 (m, 1H, C=OCH2CH2); 13C NMR (151 MHz, CDCl3) δ 170.0, 137.0, 128.5, 127.9, 127.3, 64.3, 50.3, 49.8, 36.4, 31.1, 23.8; HRMS (ES) m/z calcd for C13H18NO2 [M+H]+ 220.1338, found 220.1329.
参考文献：
[1] Chemistry - A European Journal, 2006, vol. 12, # 32, p. 8208 - 8219
[2] Amino Acids, 2013, vol. 44, # 2, p. 511 - 518
[3] Patent: WO2017/100776, 2017, A1. Location in patent: Paragraph 0143; 0145
[4] Patent: WO2018/160889, 2018, A1. Location in patent: Page/Page column 453; 454
[5] Organic and Biomolecular Chemistry, 2004, vol. 2, # 13, p. 1825 - 1826